Alkyl ethers of aliphatic alcohols are useful intermediates for a variety of specialty chemical products, including surfactants, chelants, lubricants, and functional additives. The alkyl ethers can be prepared by olefin etherification, also commonly referred to as hydroalkoxylation: an addition reaction of an alcohol to an olefin in the presence of an acid catalyst.
To date, the commercial viability of this process has been limited by low conversion of the olefin to the desired ether due in part to the instability of the ether under the reaction conditions and the tendency of some olefins, particularly aliphatic olefins, to isomerize in the presence of the catalyst and become less reactive. One consequence of this tendency is that the prior art requires the use of large excesses of reactants to achieve even marginal yields. See for example the conversion of 1-dodecene to the dichloro dodecyl ether with 1,3-dichloro-2-propanol described in Bakker et al., J. Am. Oil Chem. Soc., 1967, 44, 517-512.
It would be a significant advance in the field to provide viable olefin etherification processes that overcome the shortcomings of the prior art and in particular that provide high conversion of the starting olefin to desired product.